Np mrd loader

Showing NP-Card for Foeniculoside III (NP0049876)

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Record Information
Version2.0
Created at2022-03-17 21:19:32 UTC
Updated at2022-03-17 21:19:32 UTC
NP-MRD IDNP0049876
Secondary Accession NumbersNone
Natural Product Identification
Common NameFoeniculoside III
DescriptionFoeniculoside III belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Foeniculoside III is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Foeniculoside III has been detected, but not quantified in, fennels and herbs and spices. This could make foeniculoside III a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049876 (Foeniculoside III)


  Mrv0541 05061312452D          

 73 82  0  0  0  0            999 V2000
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M  END
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3D MOL for NP0049876 (Foeniculoside III)

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3D SDF for NP0049876 (Foeniculoside III)

  Mrv0541 05061312452D          

 73 82  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0049876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC3=C(C(C(O3)C3=CC=C(O)C=C3)C3=CC(OC4OC(CO)C(O)C(O)C4O)=CC(O)=C3)C(=C2)C2C(OC3=C2C(\C=C\C2=CC=C(O)C=C2)=CC(O)=C3)C2=CC=C(O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C54H52O19/c55-22-39-45(62)47(64)49(66)53(72-39)68-34-17-28(16-32(60)18-34)42-43-36(20-35(69-54-50(67)48(65)46(63)40(23-56)73-54)21-38(43)71-51(42)25-5-11-30(58)12-6-25)44-41-27(4-1-24-2-9-29(57)10-3-24)15-33(61)19-37(41)70-52(44)26-7-13-31(59)14-8-26/h1-21,39-40,42,44-67H,22-23H2/b4-1+

> <INCHI_KEY>
VAKPECSFQPSYGO-DAFODLJHSA-N

> <FORMULA>
C54H52O19

> <MOLECULAR_WEIGHT>
1004.9793

> <EXACT_MASS>
1004.310279482

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
101.55184913492317

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({4-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-3-(3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-6-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
3.982461867000001

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.14702242692916

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.747801831534893

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6789465892609448

> <JCHEM_POLAR_SURFACE_AREA>
318.37

> <JCHEM_REFRACTIVITY>
256.9123

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({4-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-3-(3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-6-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049876 (Foeniculoside III)
Download
PDB for NP0049876 (Foeniculoside III)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
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HETATM   48  C   UNK     0       5.292   6.432   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.877   4.941   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       7.193   8.308   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       7.463  -0.939   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -6.842  -4.720   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -8.329  -5.124   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -8.721  -6.613   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -7.628  -7.698   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -6.142  -7.294   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -5.750  -5.805   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -10.207  -7.018   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0     -11.301  -5.933   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      -4.263  -5.401   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      -5.049  -8.379   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      -8.021  -9.187   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       2.786   4.880   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       1.453   5.651   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       1.453   7.191   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       2.787   7.960   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       4.120   7.190   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0       4.120   5.650   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0       5.454   7.960   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0       5.455   9.500   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0       0.119   4.881   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0       2.787   9.500   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0       0.119   7.961   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    3                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12   16                                                  
CONECT   12    8   11                                                       
CONECT   13   10   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   11   15                                                       
CONECT   17    9   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   17   21                                                       
CONECT   23   15   63                                                       
CONECT   24   19   52                                                       
CONECT   25   21                                                            
CONECT   26   13   27   30                                                  
CONECT   27   26   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   26   29   34                                                  
CONECT   31   29   32                                                       
CONECT   32   31   33   51                                                  
CONECT   33   32   34                                                       
CONECT   34   30   33   42                                                  
CONECT   35   27   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   35   39                                                       
CONECT   41   38                                                            
CONECT   42   34   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48   50                                                  
CONECT   48   47   49                                                       
CONECT   49   44   48                                                       
CONECT   50   47                                                            
CONECT   51   32                                                            
CONECT   52   24   53   57                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55   58                                                  
CONECT   55   54   56   62                                                  
CONECT   56   55   57   61                                                  
CONECT   57   52   56   60                                                  
CONECT   58   54   59                                                       
CONECT   59   58                                                            
CONECT   60   57                                                            
CONECT   61   56                                                            
CONECT   62   55                                                            
CONECT   63   23   64   68                                                  
CONECT   64   63   65   71                                                  
CONECT   65   64   66   73                                                  
CONECT   66   65   67   72                                                  
CONECT   67   66   68   69                                                  
CONECT   68   63   67                                                       
CONECT   69   67   70                                                       
CONECT   70   69                                                            
CONECT   71   64                                                            
CONECT   72   66                                                            
CONECT   73   65                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  164    0
END

Download
3D PDB for NP0049876 (Foeniculoside III)
Download
SMILES for NP0049876 (Foeniculoside III)
OCC1OC(OC2=CC3=C(C(C(O3)C3=CC=C(O)C=C3)C3=CC(OC4OC(CO)C(O)C(O)C4O)=CC(O)=C3)C(=C2)C2C(OC3=C2C(\C=C\C2=CC=C(O)C=C2)=CC(O)=C3)C2=CC=C(O)C=C2)C(O)C(O)C1O
Download
INCHI for NP0049876 (Foeniculoside III)
InChI=1S/C54H52O19/c55-22-39-45(62)47(64)49(66)53(72-39)68-34-17-28(16-32(60)18-34)42-43-36(20-35(69-54-50(67)48(65)46(63)40(23-56)73-54)21-38(43)71-51(42)25-5-11-30(58)12-6-25)44-41-27(4-1-24-2-9-29(57)10-3-24)15-33(61)19-37(41)70-52(44)26-7-13-31(59)14-8-26/h1-21,39-40,42,44-67H,22-23H2/b4-1+
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC54H52O19
Average Mass1004.9793 Da
Monoisotopic Mass1004.31028 Da
IUPAC Name2-({4-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-3-(3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-6-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name2-({4-[6-hydroxy-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-3-(3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-6-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry Number168010-12-6
SMILES
OCC1OC(OC2=CC3=C(C(C(O3)C3=CC=C(O)C=C3)C3=CC(OC4OC(CO)C(O)C(O)C4O)=CC(O)=C3)C(=C2)C2C(OC3=C2C(\C=C\C2=CC=C(O)C=C2)=CC(O)=C3)C2=CC=C(O)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=1S/C54H52O19/c55-22-39-45(62)47(64)49(66)53(72-39)68-34-17-28(16-32(60)18-34)42-43-36(20-35(69-54-50(67)48(65)46(63)40(23-56)73-54)21-38(43)71-51(42)25-5-11-30(58)12-6-25)44-41-27(4-1-24-2-9-29(57)10-3-24)15-33(61)19-37(41)70-52(44)26-7-13-31(59)14-8-26/h1-21,39-40,42,44-67H,22-23H2/b4-1+
InChI KeyVAKPECSFQPSYGO-DAFODLJHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Foeniculum vulgareFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
Class2-arylbenzofuran flavonoids  
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids  
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
    • 

  • Stilbene glycoside
    • 

  • 1-phenylcoumaran
    • 

  • Phenolic glycoside
    • 

  • Stilbene
    • 

  • O-glycosyl compound
    • 

  • Glycosyl compound
    • 

  • Coumaran
    • 

  • Styrene
    • 

  • Phenoxy compound
    • 

  • Phenol ether
    • 

  • Phenol
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Monosaccharide
    • 

  • Benzenoid
    • 

  • Oxane
    • 

  • Monocyclic benzene moiety
    • 

  • Secondary alcohol
    • 

  • Acetal
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Polyol
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.51ALOGPS
logP3.98ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8.75ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area318.37 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity256.91 m³·mol⁻¹ChemAxon
Polarizability101.55 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0041557  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021542  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131753167  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available